Synthetic Exploration of Novel Sulfamoyl Cyanide N‐Oxides in Heterocycle Synthesis. Issue 46 (8th December 2022)

• Record Type: Journal Article
• Authors: Krivovicheva, Vasilisa; Bubyrev, Andrey; Kalinin, Stanislav; Dar'in, Dmitry; Krasavin, Mikhail
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-08
• Subjects: CH-diazomethane sulfonamides -- Cycloaddition -- Dimerization -- Nitrile oxides -- tert-Butyl nitrite; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201162
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Treatment of CH‐diazomethane sulfonamides with tert ‐butyl nitrite produces novel sulfamoyl cyanide N ‐oxides which dimerize to form furoxanes. When the reaction is performed in the presence of a dipolarophile, an olefin or an alkyne, dipolar cycloaddition takes place to deliver isoxazolines or isoxazoles, respectively. Abstract : The earlier introduced CH‐diazomethane sulfonamides were transformed into sulfamoyl cyanide N ‐oxides. The latter dimerized to give furoxanes or underwent cycloaddition with olefins and alkynes to give isooxazolines and isoxazoles, respectively.